JP2020029416A - Arylamine compound and use thereof - Google Patents

Abstract

To provide a novel arylamine compound and an organic EL element that is high in luminous efficiency and excellent in durability.SOLUTION: Provided is an arylamine compound represented by the following formula (E85).SELECTED DRAWING: None

Description

  The present invention relates to a novel arylamine compound and an organic EL device using the same.

  The organic EL element is a surface-emitting element in which an organic thin film is sandwiched between a pair of electrodes, and has features such as thinness and lightness, a high viewing angle, and high-speed response, and is expected to be applied to various display elements. . In recent years, some practical applications, such as displays for mobile phones, have begun. An organic EL element is an element that utilizes light emitted when holes injected from an anode and electrons injected from a cathode recombine in a light-emitting layer, and has a structure including a hole-transport layer and a light-emitting layer. The mainstream is a multilayer laminate type in which an electron transport layer and the like are laminated. Here, the charge transport layers such as the hole transport layer and the electron transport layer do not themselves emit light, but facilitate the charge injection into the light emitting layer, and the charge injected into the light emitting layer and the light emitting layer. It plays a role of confining the energy of the generated excitons. Therefore, the charge transport layer is very important for lowering the driving voltage and improving the luminous efficiency of the organic EL device.

  As the hole transport material, an arylamine compound having an appropriate ionization potential and hole transport ability is used. As such an amine compound, 4,4′-bis [N- (1-naphthyl) -N-phenylamino Biphenyl (hereinafter abbreviated as NPD) is widely recognized as a standard material (for example, Non-Patent Document 1). However, NPD has a problem in element life since the glass transition temperature is not sufficiently high. Further, the driving voltage and the luminous efficiency of the device using NPD for the hole transport layer were not enough to satisfy the market demand.

  Against this background, the development of arylamine compounds having a condensed ring capable of ensuring a high glass transition temperature and having an excellent hole transporting property has been promoted.

  As one of condensed rings that can ensure a high glass transition temperature, a structure in which a benzothiophene ring or a benzofluorene ring is fused to a phenanthrene ring is known, and a hole transport material using such a condensed ring has also been reported. (For example, see Patent Documents 1 and 2). However, these compounds are not optimal in the mode of introducing the amino group, which is the most important in the hole transport material, and there is room for improvement in the characteristics when used in an organic EL device.

  From such a background, in order to solve the above-mentioned problems, a hole transporting material having excellent element life and luminous efficiency, and an organic EL element using the same are required.

International Publication No. WO2012 / 045710 International Publication No. 2013/055512

Applied Physics Letters, 1996, 69, 2160.

  An object of the present invention is to provide an arylamine compound which is more excellent in device life and luminous efficiency than conventionally known arylamine compounds, and an organic EL device using the arylamine compound.

  The present inventors have conducted intensive studies and found that the following general formula (1) having a benzo [b] phenanthreno [9,10-d] thiophene ring or a benzo [b] phenanthreno [9,10-d] furan ring in the molecule. The arylamine compound represented by the formula (1) was found to be superior in the device life and luminous efficiency of the organic EL device as compared with conventionally known amine compounds, and completed the present invention.

(In the formula, X represents an oxygen atom or a sulfur atom.
L is a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms [these Are each independently a methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or 3 to 18 carbon atoms. Cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, 6 to 18 carbon atoms A monocyclic, linked or condensed aryloxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a C18 to C40 From triarylsilyl, cyano, halogen and deuterium atoms That represents the more the substituents may be one or more selected] group.
Ar ^{1 to} Ar ³ each independently represent a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked or condensed heterocyclic group having 3 to 20 carbon atoms. Aromatic group [These groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A chain, branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, A monocyclic, linked, or fused aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked, or fused heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, carbon A triarylsilyl group, a cyano group, and a halogen atom represented by Formulas 18 to 40 And it represents deuterium consisting atom a substituent selected from the group may have one or more.
R ^{1 to} R ³ each independently represent a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 20 carbon atoms, a monocyclic, linked, or fused heteroaromatic having 3 to 20 carbon atoms. Group [These groups each independently represent a methyl group, an ethyl group, a linear or branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, carbon A monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a carbon number 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and heavy May have one or more substituents selected from the group consisting of elemental atoms], a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, and an ethoxy group. A linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, carbon number Represents a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )
That is, the present invention relates to an arylamine compound represented by the above general formula (1) and its use.

  The organic EL device using the arylamine compound of the present invention exhibited a high luminous efficiency (current efficiency) and a low driving voltage as compared with conventionally known materials, and further exhibited a remarkable effect of excellent device life.

  According to the present invention, it is possible to provide an organic EL device having high luminance and efficiency, high durability, and long life.

  Hereinafter, the present invention will be described in detail.

  The present invention relates to the arylamine compound represented by the general formula (1).

  The definition and the preferred range of each group in the general formula (1) are as described below.

  In the compound represented by the general formula (1) of the present invention, a triarylamine is added to a benzo [b] phenanthreno [9,10-d] thiophene ring or a benzo [b] phenanthreno [9,10-d] furan ring. It is characterized in that there is one amine substituent having a substituent. The substitution position of the amine substituent is preferably a substitution position represented by the following general formulas (2) to (5) in consideration of the planarity of the molecule.

(In the formula, X, L, Ar ^{1 to} Ar ³ , and R ^{1 to} R ³ have the same meaning as in the general formula (1).)
In the general formulas (1) to (5), X represents an oxygen atom or a sulfur atom. X is preferably a sulfur atom in terms of excellent durability, and an oxygen atom is preferred in terms of excellent luminous efficiency.

  In the general formulas (1) to (5), L represents a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked, or linked, having 3 to 20 carbon atoms. Condensed divalent heteroaromatic groups [these groups each independently represent a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, A straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic ring having 6 to 20 carbon atoms, connection, or A condensed aryl group, a C6-C18 monocyclic, linked or condensed aryloxy group, a C3-C20 monocyclic, linked or condensed heteroaryl group, a C3-C18 A trialkylsilyl group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, It represents a Gen atom, and a substituent selected from the group consisting of heavy hydrogen atoms may have one or more.

  Examples of the monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms in L include, but are not particularly limited to, for example, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, Phenylnaphthalene-diyl group, binaphthylene group, fluorene-diyl group, benzofluorene-diyl group, phenanthrene-diyl group, fluoranthene-diyl group, anthracene-diyl group, chrysene-diyl group, pyrene-diyl group, triphenylene-diyl group, Or a perylene-diyl group.

  The monovalent, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms in L is not particularly limited, and includes, for example, at least one oxygen atom, nitrogen atom, or sulfur atom Examples thereof include a monocyclic, linked or condensed divalent heteroaromatic group having 3 to 20 carbon atoms, which is not particularly limited. For example, a pyrrole-diyl group, a thiophene-diyl group, a furan- Diyl group, imidazole-diyl group, thiazole-diyl group, isothiazole-diyl group, oxazole-diyl group, isoxazole-diyl group, pyridine-diyl group, pyrimidine-diyl group, pyrazine-diyl group, triazine-idyl group, Indole-diyl group, benzothiophene-diyl group, benzofuran-diyl group, benzimidazole-diyl group, benzothiazo Ru-diyl group, benzoisothiazole-diyl group, 2,1,3-benzothiadiazole-diyl group, benzoxazole-diyl group, benzoisoxazole-diyl group, 2,1,3-benzoxadiazol-diyl group Thienothiophene-diyl group, dithienothiophene-diyl group, benzodithiophene-diyl group, quinoline-diyl group, isoquinoline-diyl group, quinoxaline-diyl group, phenanthroline-diyl group, dibenzothiophene-diyl group, benzothienobenzo Thiophene-diyl group, dibenzofuran-diyl group, carbazole-diyl group, phenoxazine-diyl group, phenothiazine-diyl group, thiantrene-diyl group, phenylthiophen-diyl group, diphenylthiophen-diyl group, phenylfuran-diyl , Diphenyl furan - diyl group, bithiophene - diyl group, terthiophene - diyl group, phenylpyridine - diyl group, or a bipyridine - diyl group, and the like.

  Hereinafter, a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms and a monocyclic, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms in L are The definition of the substituent which may be possessed is shown below.

  Although it does not specifically limit as a C3-C18 linear, branched, or cyclic alkyl group, For example, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group Hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.

  The straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group. , A pentyloxy group, a hexyloxy group, or a stearyloxy group.

  The halogenated alkyl group having 1 to 3 carbon atoms is not particularly limited, and examples thereof include a trifluoromethyl group, a trichloromethyl group, and a 2-fluoroethyl group.

  The halogenated alkoxy group having 1 to 3 carbon atoms is not particularly limited, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, and a 2-fluoroethoxy group.

  The monocyclic, linked, or condensed aryl group having 6 to 20 carbon atoms is a monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. The group is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, and a 3-methoxyphenyl group. Methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, biphenyl group, naphthyl group, Examples thereof include a 1-methylnaphthyl group, a 2-methylnaphthyl group, a 1-methoxynaphthyl group, a 2-methoxynaphthyl group, and a 9,9-dimethylfluorenyl group.

  The monocyclic, linked, or condensed aryloxy group having 6 to 18 carbon atoms is not particularly limited, and examples thereof include a phenoxy group, a 2-methylphenoxy group, a 3-methylphenoxy group, and a 4-methylphenoxy group. Group, 2-methoxyphenoxy group, 3-methoxyphenoxy group, 4-methoxyphenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanophenoxy group, 3,4-dimethylphenoxy group, 2,6- Examples include a dimethylphenoxy group, a biphenyloxy group, and a naphthyloxy group.

  The monocyclic, linked, or condensed heteroaryl group having 3 to 20 carbon atoms is a monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms which may have a substituent. The group is not particularly limited, and examples thereof include a pyrrolyl group, a 1-methylpyrrolyl group, a 1-phenylpyrrolyl group, a thienyl group, a 2-methylthienyl group, and a 2-cyanothienyl group. , 2-phenylthienyl group, furyl group, 2-phenylfuryl group, imidazolyl group, 1-methylimidazolyl group, 2-methylimidazolyl group, 1-phenylimidazolyl group, 2-phenyl-imidazolyl group, pyrazolyl group, thiazolyl group, Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 2,4-diph Nyl-1,3,5-triazyl group, indolyl group, benzothienyl group, benzofuranyl group, benzimidazolyl group, 2-methylbenzimidazolyl group, 2-phenylbenzimidazolyl group, 1-methylbenzimidazolyl group, 1-phenylbenzimidazolyl group, 1, 2-diphenylbenzimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzo Oxadiazolyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, carbazolyl group, 9-methylcarbazolyl group, 9-ethylcarbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, dibenzofura Nil group, phenoxadi Group, phenothiazinyl group, acridinyl group, phenanthroline group, phenazine group, or thianthrenyl group.

  The trialkylsilyl group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, and a tributylsilyl group.

  Examples of the triarylsilyl group having 18 to 40 carbon atoms include, but are not particularly limited to, a triphenylsilyl group, a tri (2-methylphenyl) silyl group, a tri (3-methylphenyl) silyl group, and a tri ( Examples thereof include a 4-methylphenyl) silyl group and a tri (4-biphenylyl) silyl group.

  Examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

Specific examples of L include, but are not particularly limited to, for example, 1,4-phenylene group, 2-methyl-1,4-phenylene group, 2-ethyl-1,4-phenylene group, 2-n- Propyl-1,4-phenylene group, 2-isopropyl-1,4-phenylene group, 2-n-butyl-1,4-phenylene group, 2-n-hexyl-1,4-phenylene group, 2-n- Octyl-1,4-phenylene group, 1,3-phenylene group, 5-methyl-1,3-phenylene group, 5-ethyl-1,3-phenylene group, 5-n-propyl-1,3-phenylene group , 5-isopropyl-1,3-phenylene group, 5-n-butyl-1,3-phenylene group, 5-n-hexyl-1,3-phenylene group, 5-n-octyl-1,3-phenylene group A 2-methyl-1,3-phenylene group, -Ethyl-1,3-phenylene group, 4-methyl-1,3-phenylene group, 4-ethyl-1,3-phenylene group, 1,2-phenylene group, 4-methyl-1,2-phenylene group, 4-ethyl-1,2-phenylene group, 4-n-propyl-1,2-phenylene group, 4-isopropyl-1,2-phenylene group, 4-n-butyl-1,2-phenylene group, 4- n-hexyl-1,2-phenylene group, 4-n-octyl-1,2-phenylene group, 3-methyl-1,2-phenylene group, 3-ethyl-1,2-phenylene group, 3,6- Dimethyl-1,4-phenylene group, 3,6-diethyl-1,4-phenylene group, 3,6-di-n-butyl-1,4-phenylene group, 3,6-di-n-hexyl-1 , 4-phenylene group, 3,6-di-n-octyl-1,4- Phenylene group, 2,3-dimethyl-1,4-phenylene group, 2,3-diethyl-1,4-phenylene group, 2-methoxy-1,4-phenylene group, 2-ethoxy-1,4-phenylene group , 2-n-propyloxy-1,4-phenylene group, 2-isopropyloxy-1,4-phenylene group, 2-n-butoxy-1,4-phenylene group, 2-n-hexyloxy-1,4 -Phenylene group, 2-n-octyloxy-1,4-phenylene group, 5-methoxy-1,3-phenylene group, 5-ethoxy-1,3-phenylene group, 5-n-propyloxy-1,3 -Phenylene group, 5-isopropyloxy-1,3-phenylene group, 5-n-butoxy-1,3-phenylene group, 5-n-hexyloxy-1,3-phenylene group, 5-n-octyloxy- 1, 3-phenylene group, 2-methoxy-1,3-phenylene group, 2-ethoxy-1,3-phenylene group, 4-methoxy-1,3-phenylene group, 4-ethoxy-1,3-phenylene group, 4 -Methoxy-1,2-phenylene group, 4-ethoxy-1,2-phenylene group, 4-n-propyloxy-1,2-phenylene group, 4-isopropyloxy-1,2-phenylene group, 4-n -Butoxy-1,2-phenylene group, 4-n-hexyloxy-1,2-phenylene group, 4-n-octyloxy-1,2-phenylene group, 3-methoxy-1,2-phenylene group, 3 -Ethoxy-1,2-phenylene group, 3,6-diethoxy-1,4-phenylene group, 3,6-diethoxy-1,4-phenylene group, 3,6-di-n-butoxy-1,4- Phenylene group, 3,6 Di-n-hexyloxy-1,4-phenylene group, 3,6-di-n-octyloxy-1,4-phenylene group, 2,3-dimethoxy-1,4-phenylene group, 2,3-diethoxy -1,4-phenylene group, 2-cyano-1,4-phenylene group, 5-cyano-1,3-phenylene group, 2-cyano-1,3-phenylene group, 4-cyano-1,3-phenylene Group, 4-cyano-1,2-phenylene group, 3-cyano-1,2-phenylene group, 3,6-dicyano-1,4-phenylene group, 2,3-dicyano-1,4-phenylene group, 2,5-dicyano-1,3-phenylene group, 2,4-dicyano-1,3-phenylene group, 4,5-dicyano-1,3-phenylene group, 3,4-dicyano-1,2-phenylene Group, 4,5-dicyano-1,2-phenylene , 2-fluoro-1,4-phenylene group, 5-fluoro-1,3-phenylene group, 2-fluoro-1,3-phenylene group, 4-fluoro-1,3-phenylene group, 4-fluoro-1 , 2-phenylene group, 3-fluoro-1,2-phenylene group, 3,6-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 2,5-difluoro-1 , 3-phenylene group, 2,4-difluoro-1,3-phenylene group, 4,5-difluoro-1,3-phenylene group, 3,4-difluoro-1,2-phenylene group, 4,5-difluoro -1,2-phenylene group, 4,4'-biphenylene group, 3,4'-biphenylene group, 2,4'-biphenylene group, 3,3'-biphenylene group, 3,2'-biphenylene group, 2, 2′-biphenylene group, 2-me Tyl-4,4'-biphenylene group, 3-methyl-4,4'-biphenylene group, 2,2'-dimethyl-4,4'-biphenylene group, 3,3'-dimethyl-4,4'-biphenylene Group, 2,3′-dimethyl-4,4′-biphenylene group, 3,5-dimethyl-4,4′-biphenylene group, 3,6-dimethyl-4,4′-biphenylene group, 2,5-dimethyl -4,4'-biphenylene group, 2,6-dimethyl-4,4'-biphenylene group, 2,5,2 ', 5'-tetramethyl-4,4'-biphenylene group, 2,6,2' , 6′-tetramethyl-4,4′-biphenylene group, 3,5,3 ′, 5′-tetramethyl-4,4′-biphenylene group, 2-methoxy-4,4′-biphenylene group, 3- Methoxy-4,4′-biphenylene group, 2,2′-dimethoxy-4,4′-biphenylene group, 3,3 ′ Dimethoxy-4,4'-biphenylene group, 2,3'-dimethoxy-4,4'-biphenylene group, 3,5-dimethoxy-4,4'-biphenylene group, 3,6-dimethoxy-4,4'- Biphenylene group, 2,5-dimethoxy-4,4'-biphenylene group, 2,6-dimethoxy-4,4'-biphenylene group, 2,5,2 ', 5'-tetramethoxy-4,4'-biphenylene Group, 2,6,2 ', 6'-tetramethoxy-4,4'-biphenylene group, 2,2'-ditrifluoromethyl-4,4'-biphenylene group, 2-fluoro-4,4'-biphenylene Group, 3-fluoro-4,4'-biphenylene group, 2,2'-difluoro-4,4'-biphenylene group, 3,3'-difluoro-4,4'-biphenylene group, 2,3'-difluoro -4,4'-biphenylene group, 3,5-difluoro- , 4'-biphenylene group, 3,6-difluoro-4,4'-biphenylene group, 2,5-difluoro-4,4'-biphenylene group, 2,6-difluoro-4,4'-biphenylene group, 2 , 5,2 ', 5'-tetrafluoro-4,4'-biphenylene group, 2,6,2', 6'-tetrafluoro-4,4'-biphenylene group, 2-cyano-4,4'- Biphenylene group, 3-cyano-4,4'-biphenylene group, 2,2'-dicyano-4,4'-biphenylene group, 3,3'-dicyano-4,4'-biphenylene group, 2,3'- Dicyano-4,4'-biphenylene group, 3,5-dicyano-4,4'-biphenylene group, 3,6-dicyano-4,4'-biphenylene group, 2,5-dicyano-4,4'-biphenylene Group, 2,6-dicyano-4,4′-biphenylene group, 2,5,2 ′, 5′- Tracyano-4,4'-biphenylene group, 2,6,2 ', 6'-tetracyano-4,4'-biphenylene group, 2-phenyl-4,4'-biphenylene group, 3-phenyl-4,4' -Biphenylene group,
2,2'-diphenyl-4,4'-biphenylene group, 3,3'-diphenyl-4,4'-biphenylene group, 2,3'-diphenyl-4,4'-biphenylene group, 3,5-diphenyl -4,4'-biphenylene group, 3,6-diphenyl-4,4'-biphenylene group, 2,5-diphenyl-4,4'-biphenylene group, 2,6-diphenyl-4,4'-biphenylene group 2,5,2 ′, 5′-tetraphenyl-4,4′-biphenylene group, 2,6,2 ′, 6′-tetraphenyl-4,4′-biphenylene group, 2-methyl-3,4 '-Biphenylene group, 4-methyl-3,4'-biphenylene group, 5-methyl-3,4'-biphenylene group, 6-methyl-3,4'-biphenylene group, 2'-methyl-3,4' -Biphenylene group, 3'-methyl-3,4'-biphenylene group, 2,2'-dimethyl 3,4'-biphenylene group, 4,2'-dimethyl-3,4'-biphenylene group, 5,2'-dimethyl-3,4'-biphenylene group, 6,2'-dimethyl-3,4 A '-biphenylene group, a 2,3'-dimethyl-3,4'-biphenylene group, a 4,3'-dimethyl-3,4'-biphenylene group, a 5,3'-dimethyl-3,4'-biphenylene group, 6,3′-dimethyl-3,4′-biphenylene group, 2-methoxy-3,4′-biphenylene group, 4-methoxy-3,4′-biphenylene group, 5-methoxy-3,4′-biphenylene group , 6-methoxy-3,4'-biphenylene group, 2'-methoxy-3,4'-biphenylene group, 3'-methoxy-3,4'-biphenylene group, 2,2'-dimethoxy-3,4 ' -Biphenylene group, 4,2'-dimethoxy-3,4'-biphenylene group, 5,2'-di Methoxy-3,4'-biphenylene group, 6,2'-dimethoxy-3,4'-biphenylene group, 2,3'-dimethoxy-3,4'-biphenylene group, 4,3'-dimethoxy-3,4 '-Biphenylene group, 5,3'-dimethoxy-3,4'-biphenylene group, 6,3'-dimethoxy-3,4'-biphenylene group, 2-fluoro-3,4'-biphenylene group, 4-fluoro -3,4'-biphenylene group, 5-fluoro-3,4'-biphenylene group, 6-fluoro-3,4'-biphenylene group, 2'-fluoro-3,4'-biphenylene group, 3'-fluoro -3,4'-biphenylene group, 2,2'-difluoro-3,4'-biphenylene group, 4,2'-difluoro-3,4'-biphenylene group, 5,2'-difluoro-3,4 ' -Biphenylene group, 6,2'-difluoro-3,4'-biphe A len group, a 2,3′-difluoro-3,4′-biphenylene group, a 4,3′-difluoro-3,4′-biphenylene group, a 5,3′-difluoro-3,4′-biphenylene group, 3'-difluoro-3,4'-biphenylene group, 2-cyano-3,4'-biphenylene group, 4-cyano-3,4'-biphenylene group, 5-cyano-3,4'-biphenylene group, 6 -Cyano-3,4'-biphenylene group, 2'-cyano-3,4'-biphenylene group, 3'-cyano-3,4'-biphenylene group, 2,2'-dicyano-3,4'-biphenylene Group, 4,2′-dicyano-3,4′-biphenylene group, 5,2′-dicyano-3,4′-biphenylene group, 6,2′-dicyano-3,4′-biphenylene group, 2,3 '-Dicyano-3,4'-biphenylene group, 4,3'-dicyano-3,4'-biphenylene Group, 5,3′-dicyano-3,4′-biphenylene group, 6,3′-dicyano-3,4′-biphenylene group, 2-phenyl-3,4′-biphenylene group, 4-phenyl-3, 4′-biphenylene group, 5-phenyl-3,4′-biphenylene group, 6-phenyl-3,4′-biphenylene group, 2′-phenyl-3,4′-biphenylene group, 3′-phenyl-3, 4'-biphenylene group, 2,2'-diphenyl-3,4'-biphenylene group, 4,2'-diphenyl-3,4'-biphenylene group, 5,2'-diphenyl-3,4'-biphenylene group , 6,2'-diphenyl-3,4'-biphenylene group, 2,3'-diphenyl-3,4'-biphenylene group, 4,3'-diphenyl-3,4'-biphenylene group, 5,3 '-Diphenyl-3,4'-biphenylene group, 6,3'-diphenyl-3 4'-biphenylene group, 2-methyl-3,3'-biphenylene group, 4-methyl-3,3'-biphenylene group, 5-methyl-3,3'-biphenylene group, 6-methyl-3,3 ' -Biphenylene group, 2,2'-dimethyl-3,3'-biphenylene group, 4,4'-dimethyl-3,3'-biphenylene group, 2,4'-dimethyl-3,3'-biphenylene group, , 5′-dimethyl-3,3′-biphenylene group, 2,6-dimethyl-3,3′-biphenylene group, 2,5-dimethyl-3,3′-biphenylene group, 2,4-dimethyl-3, 3′-biphenylene group, 2,4,2 ′, 4′-tetramethyl-3,3′-biphenylene group, 2,5,2 ′, 5′-tetramethyl-3,3′-phenylene group, 2, 6,2 ′, 6′-tetramethyl-3,3′-biphenylene group, 2-methoxy-3,3′-biphenyl 4-methoxy-3,3'-biphenylene group, 5-methoxy-3,3'-biphenylene group, 6-methoxy-3,3'-biphenylene group, 2,2'-dimethoxy-3,3 ' -Biphenylene group, 4,4'-dimethoxy-3,3'-biphenylene group, 2,4'-dimethoxy-3,3'-biphenylene group, 2,5'-dimethoxy-3,3'-biphenylene group, , 6-Dimethoxy-3,3′-biphenylene group, 2,5-dimethoxy-3,3′-biphenylene group, 2,4-dimethoxy-3,3′-biphenylene group, 2,4,2 ′, 4 ′ -Tetramethoxy-3,3'-biphenylene group, 2,5,2 ', 5'-tetramethoxy-3,3'-biphenylene group, 2,6,2', 6'-tetramethoxy-3,3 ' -Biphenylene group, 2-cyano-3,3'-biphenylene group, 4-cyano-3, '-Biphenylene group, 5-cyano-3,3'-biphenylene group, 6-cyano-3,3'-biphenylene group, 2,2'-dicyano-3,3'-biphenylene group, 4,4'-dicyano -3,3'-biphenylene group, 2,4'-dicyano-3,3'-biphenylene group, 2,5'-dicyano-3,3'-biphenylene group, 2,6-dicyano-3,3'- Biphenylene group, 2,5-dicyano-3,3′-biphenylene group, 2,4-dicyano-3,3′-biphenylene group, 2,4,2 ′, 4′-tetracyano-3,3′-biphenylene group 2,5,2 ', 5'-tetracyano-3,3'-biphenylene group, 2,6,2', 6'-tetracyano-3,3'-biphenylene group, 2-fluoro-3,3'- Biphenylene group, 4-fluoro-3,3'-biphenylene group, 5-fluoro-3,3'-biph Nylene group, 6-fluoro-3,3'-biphenylene group, 2,2'-difluoro-3,3'-biphenylene group, 4,4'-difluoro-3,3'-biphenylene group, 2,4'- Difluoro-3,3'-biphenylene group, 2,5'-difluoro-3,3'-biphenylene group, 2,6-difluoro-3,3'-biphenylene group, 2,5-difluoro-3,3'- Biphenylene group, 2,4-difluoro-3,3′-biphenylene group, 2,4,2 ′, 4′-tetrafluoro-3,3′-biphenylene group,
2,5,2 ′, 5′-tetrafluoro-3,3′-biphenylene group, 2,6,2 ′, 6′-tetrafluoro-3,3′-biphenylene group, 2-phenyl-3,3 ′ -Biphenylene group, 4-phenyl-3,3'-biphenylene group, 5-phenyl-3,3'-biphenylene group, 6-phenyl-3,3'-biphenylene group, 2,2'-diphenyl-3,3 A '-biphenylene group, a 4,4'-diphenyl-3,3'-biphenylene group, a 2,4'-diphenyl-3,3'-biphenylene group, a 2,5'-diphenyl-3,3'-biphenylene group, 2,6-diphenyl-3,3'-biphenylene group, 2,5-diphenyl-3,3'-biphenylene group, 2,4-diphenyl-3,3'-biphenylene group, 2,4,2 ', 4 '-Tetraphenyl-3,3'-biphenylene group, 2,5,2', 5'-tetra Phenyl-3,3′-biphenylene group, 2,6,2 ′, 6′-tetraphenyl-3,3′-biphenylene group, 4,4 ″ -p-terphenylene group, 3,4 ″ -p -Terphenylene group, 2,4 "-p-terphenylene group, 3,3" -p-terphenylene group, 2,3 "-p-terphenylene group, 2,2" -p-ter Phenylene group, 4,4 "-m-terphenylene group, 3,4" -m-terphenylene group, 2,4 "-p-terphenylene group, 3,3" -m-terphenylene group 2,3 ″ -m-terphenylene group, 2,2 ″ -m-terphenylene group, 4,4 ″ -o-terphenylene group, 3,4 ″ -o-terphenylene group, 2 , 4 ″ -o-terphenylene group, 3,3 ″ -o-terphenylene group, 2,3 ″ -o-terphenylene group, 2,2 ″ -o-terphenylene group, 1,4 − Phthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 2,7-naphthylene group, 1-phenylnaphthalene-diyl group, 2-phenylnaphthalene-diyl group, 9,9-dimethylfluorene-2,7 -Diyl group, 9,9-dioctylfluorene-2,7-diyl group, 9,9-diphenylfluorene-2,7-diyl group, 9,9′-spirobifluorene-2,7-diyl group, 11, 11′-dimethylbenzo [a] fluorene-3,9-diyl group, 11,11′-dimethylbenzo [a] fluorene-2,9-diyl group, 11,11′-dimethylbenzo [b] fluorene-3, 9-diyl group, 11,11′-dimethylbenzo [c] fluorene-2,9-diyl group, fluoranthene-3,8-diyl group, pyrene-1,6-diyl group, pyrene-2,3-diyl Group, pyrene-2,7-diyl group, pyrene-1,8-diyl group, anthracene-2,6-diyl group, anthracene-1,5-diyl group, anthracene-9,10-diyl group, triphenylene-2 , 7-diyl group, chrysene-2,8-diyl group, pyrrole-2,5-diyl group, 1-methylpyrrole-2,5-diyl group, 1-phenylpyrrole-2,5-diyl group, thiophene- 2,5-diyl group, 3-hexylthiophene-2,5-diyl group, 3,4-ethylenedioxythiophene-2,5-diyl group, thiophene-3,4-diyl group, furan-2,5- Diyl group, furan-3,4-diyl group, thiazole-diyl group, isothiazole-diyl group, oxazole-diyl group, isoxazole-diyl group, pyridine-2,5-diyl group, pyridi -2,6-diyl group, pyrazine-2,5-diyl group, triazine-2,4-diyl group, benzothiophene-diyl group, benzofuran-diyl group, benzothiazole-diyl group, benzoisothiazole-diyl group, 2,1,3-benzothiadiazole-diyl group, benzoxazole-diyl group, benzisoxazole-diyl group, 2,1,3-benzoxadiazol-diyl group, thieno [3,2-b] thiophene-2 , 5-diyl group, thieno [3,2-b] thiophene-3,6-diyl group, dithieno [3,2-b: 2 ′, 3′-c] thiophene-2,6-diyl group, benzodi Thiophene-diyl group, dibenzothiophene-2,8-diyl group, 9-methylcarbazole-2,7-diyl group, 9-phenylcarbazole-2,7-diyl group, 9 Biphenylcarbazole-2,7-diyl group, 9-naphthylcarbazole-2,7-diyl group, 9-methylcarbazole-3,6-diyl group, 9-phenylcarbazole-3,6-diyl group, 9-biphenylcarbazole -3,6-diyl group, 9-naphthylcarbazole-3,6-diyl group, benzothienobenzothiophene-2,7-diyl group, dibenzofuran-2,8-diyl group, 10-methylphenoxazine-3,7 -Diyl group, 10-phenylphenoxazine-3,7-diyl group, 10-methylphenothiazine-3,7-diyl group, 10-phenylphenothiazine-3,7-diyl group, thianthrene-1,9-diyl group, Thianthrene-2,7-diyl group, 2-phenylthiophene-diyl group, 2,5-diphenylthiophene-diyl Group, 2-phenylfuran-diyl group, 2,5-diphenylfuran-diyl group, 2,2′-bithiophen-5,5′-diyl group, 2,2′-bithiophen-3,3′-diyl group, Alternatively, a terthiophene-5,5 ″ -diyl group and the like can be exemplified, but the invention is not limited thereto.

  L is a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracene-diyl group, or a fluorene-diyl group (each of these groups independently represents a methyl group An ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, Halogenated alkyl group, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 18 carbon atoms An oxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, and halogen And may have one or more substituents selected from the group consisting of a hydrogen atom and a deuterium atom), 1,4-phenylene group, 1,3-phenylene group, 4,4′- Biphenylene group, 3,3′-biphenylene group, 3,4′-biphenylene group, 4,4 ″ -p-terphenylene group, 4,4 ″ -m-terphenylene group, 2,6-naphthylene group, Or a fluorene-2,7-diyl group (each of these groups independently represents a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, A straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic ring having 6 to 20 carbon atoms, connection, or Condensed aryl group, monocyclic ring having 6 to 18 carbon atoms, Or a condensed aryloxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, May have one or more substituents selected from the group consisting of a cyano group, a halogen atom, and a deuterium atom), and more preferably a 1,4-phenylene group, a 1,3-phenylene group, Or it is more preferably a 4,4′-biphenylene group.

In the general formulas (1) to (5), Ar ^{1 to} Ar ³ each independently represent a monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms, or 3 to 20 carbon atoms. A monocyclic, linked, or condensed heteroaromatic group [these groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, or a methoxy group; An ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, Ring, linked or condensed aryl group, monocyclic having 6 to 18 carbon atoms, linked or condensed aryloxy group, monocyclic, connected or condensed heteroaryl group having 3 to 20 carbon atoms, carbon A trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl having 18 to 40 carbon atoms Group, a cyano group, a halogen atom, and a substituent selected from the group consisting of heavy hydrogen atoms may have one or more.

The monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms in Ar ^{1 to} Ar ³ is not particularly limited. Examples thereof include a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. Group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, anthryl group, chrysenyl group, pyrenyl group, triphenylene group, or perylenyl group.

The monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms in Ar ^{1 to} Ar ³ is not particularly limited. For example, at least one oxygen atom, nitrogen atom, or sulfur atom And a monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms, which includes, but is not particularly limited to, for example, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, Pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazyl, 1,3,5-triazyl, indolyl, benzothienyl, benzofuranyl, benzimidazolyl, indazolyl, benzothiazolyl Group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazo Group, benzoisoxazolyl group, 2,1,3-benzoxdiadialyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, carbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, pheno Examples thereof include a thiazinyl group, a phenazine group, and a thianthrenyl group.

The monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms in Ar ^{1 to} Ar ^{3 and} the monocyclic, linked or condensed heteroaromatic group having 3 to 20 carbon atoms are substituents Which may have a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, Halogenated alkyl group, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 18 carbon atoms An oxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, and a halogen atom) And the same substituents as those described above for L are exemplified. It is possible.

Specific examples of Ar ^{1 to} Ar ³ include, but are not particularly limited to, for example, phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 4-ethylphenyl, and 3-ethylphenyl. Ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl Group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4- n-decylphenyl group, 4-n-dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, -Tritylphenyl group, 3-tritylphenyl group, 4-triphenylsilylphenyl group, 3-triphenylsilylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-methoxy Phenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4 -Isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxy Phenyl, 2-sec-butoxyphenyl, 4-n-pentyloxyphenyl, 4-isopentyloxyphenyl, 2-isopentyloxyphenyl, 4-neopentyloxyphenyl, 2-neopentyloxyphenyl Group, 4-n-hexyloxyphenyl group, 2- (2-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4 -N-tetradecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5 -Methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl 5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5- Dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2 -Methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 3-cyanophenyl group, 4- Fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2, -Difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 2-methyl-1, 1'-biphenyl-4-yl group, 3-methyl-1,1'-biphenyl-4-yl group, 2'-methyl-1,1'-biphenyl-4-yl group, 3'-methyl1,1 '-Biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl -1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group 3,2′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 3′-dimethyl 1,1′-biphenyl-4-yl group, 2 ′, 4′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 5′-dimethyl-1,1′-biphenyl-4-yl Group, 2 ', 6'-dimethyl-1,1'-biphenyl-4-yl group, p-terphenyl group, m-terphenyl group, o-terphenyl group, quarterphenyl group, 1-naphthyl group, 2 -Naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 6-methylnaphthalen-2-yl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) ) Phenyl, 3- (1-naphthyl) phenyl, 3- (2-naphthyl) phenyl, 3-methyl-4- (1-naphthyl) phenyl, 3-methyl-4- (2-naphthyl) phenyl Group, 4- (2-methylnaphthalen-1-yl) phenyl Group, 3- (2-methylnaphthalen-1-yl) phenyl group, 4-phenylnaphthalen-1-yl group, 4- (2-methylphenyl) naphthalen-1-yl group, 4- (3-methylphenyl) Naphthalen-1-yl group, 4- (4-methylphenyl) naphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 4- (2-methylphenyl) naphthalen-2-yl group, 4- ( 3-methylphenyl) naphthalen-2-yl group, 4- (4-methylphenyl) naphthalen-2-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2 -Fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group, 9,9-di-n-octyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9'- S Lobifluorenyl group, 9-phenanthryl group, 2-phenanthryl group, 11,11′-dimethylbenzo [a] fluoren-9-yl group, 11,11′-dimethylbenzo [a] fluoren-3-yl group, 11,11 '-Dimethylbenzo [b] fluoren-9-yl group, 11,11'-dimethylbenzo [b] fluoren-3-yl group, 11,11'-dimethylbenzo [c] fluoren-9-yl group, 11, 11'-dimethylbenzo [c] fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-pyrenyl group, 2-pyrenyl group, 9-anthryl group, 2-anthryl group, 2 -Triphenylene group, 3-chrysenyl group, 6-chrysenyl group, 3-perylenyl group, 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl- , 4-Dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2- (2-naphthyl) -3,4-dimethyl-1-imidazolyl group, 2- (2-naphthyl) -3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl A 1-methyl-4,5-dimethyl-2-imidazolyl group, a 1-methyl-4,5-diphenyl-2-imidazolyl group, a 1-phenyl-4,5-dimethyl-2-imidazolyl group,
1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1- Methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3 -Isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3 -Methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2- Lysyl group, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group 2,2′-bipyridin-5-yl group, 2,3′-bipyridin-3-yl group, 2,3′-bipyridin-4-yl group, 2,3′-bipyridin-5-yl group, 5 -Pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2 -Phenyl-1-benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl-2-benzimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1- Tyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1-methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group , 1-methyl-2-phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl Group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzoisothiazolyl group, 4-benzoisothiazolyl group, 5-benzoisothiazolyl group , 6-benzoisothiazolyl group, 7-benzoisothi Azolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzo Oxazolyl group, 6-benzoxazolyl group, 7-benzooxazolyl group, 3-benzoisoxazolyl group, 4-benzoisoxazolyl group, 5-benzoisoxazolyl group, 6- Benzoisoxazolyl group, 7-benzoisoxazolyl group, 2,1,3-benzoxdiadialyl-4-yl group, 2,1,3-benzoxdiadialyl-5-yl group, 2- Quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2-quinoxalyl group, 6-quinoyl Salyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline -3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group , 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 2-dibenzofuranyl, 4-dibenzofuranyl, 9-methylcarbazol-2-yl, 9-methylcarbazole- 3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazole- -Yl group, 9-phenylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazol-3-yl group, 9-biphenylcarbazol-4-yl group, 2-thianthryl group, 10 -Phenylphenothiazin-3-yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group, 1-methylindol-2-yl group , 1-phenylindol-2-yl group, 9-phenylcarbazol-4-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 4- (2-pyridyl) phenyl group , 4- (3-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (2-phenylimidazol-1-yl) phenyl group, 4- (1-phenylimidazol-2-yl) phenyl group, 4- (2,3,4-triphenylimidazol-1-yl) phenyl group, 4- (1-methyl-4,5-diphenylimidazol-2-yl) phenyl group, 4- (2-methylbenzimidazol-1-yl) Yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) phenyl group, 4- (1-methylbenzimidazol-2-yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) Phenyl group, 3- (2-methylbenzimidazol-1-yl) phenyl group, 3- (2-phenylbenzimidazol-1-yl) phenyl group, 3- ( -Methylbenzimidazol-2-yl) phenyl group, 3- (2-phenylbenzimidazol-1-yl) phenyl group, 4- (3,5-diphenyltriazin-1-yl) phenyl group, 4- (2- A thienyl) phenyl group, a 4- (2-furanyl) phenyl group, a 5-phenylthiophen-2-yl group, a 5-phenylfuran-2-yl group, a 4- (5-phenylthiophen-2-yl) phenyl group, 4- (5-phenylfuran-2-yl) phenyl group, 3- (5-phenylthiophen-2-yl) phenyl group, 3- (5-phenylfuran-2-yl) phenyl group, 4- (2- Benzothienyl) phenyl group, 4- (3-benzothienyl) phenyl group, 3- (2-benzothienyl) phenyl group, 3- (3-benzothienyl) phenyl group, 4- (2-di Benzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 3- (2-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (2-dibenzofuranyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 3- (2-dibenzofuranyl) phenyl group, 3- (4-dibenzofuranyl) phenyl group, 5-phenylpyridin-2-yl group, 4-phenylpyridine Examples thereof include a 2-yl group, a 5-phenylpyridin-3-yl group, a 4- (9-carbazolyl) phenyl group, and a 3- (9-carbazolyl) phenyl group, but are not limited thereto. Not something.

Ar ^{1 to} Ar ³ each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a benzofluorenyl group; A dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group, a carbazolylphenyl group, a dibenzothienylphenyl group, or a dibenzofuranylphenyl group (these groups each independently represent a methyl group, an ethyl group, a carbon number of 3 to 18 linear, branched, or cyclic alkyl groups, methoxy groups, ethoxy groups, 3 to 18 linear, branched, or cyclic alkoxy groups, 1 to 3 halogenated alkyl groups, 1 carbon atoms To 3 halogenated alkoxy groups, monocyclic, connected or condensed aryl groups having 6 to 20 carbon atoms, monocyclic rings having 6 to 18 carbon atoms, connected, or Condensed aryloxy group, monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group , A halogen atom, and a deuterium atom, which may have at least one substituent selected from the group consisting of phenyl, biphenyl, terphenyl, and naphthyl. Phenanthryl group, triphenylene group, fluorenyl group, dibenzothienyl group, dibenzofuranyl group, carbazolyl group, carbazolylphenyl group, dibenzothienylphenyl group, or dibenzofuranylphenyl group (these groups are each independently Methyl group, ethyl group, C 3-18 linear, branched or cyclic alkyl group, methoxy group, ethoxy group, C 3 18 straight-chain, branched or cyclic alkoxy groups, halogenated alkyl groups having 1 to 3 carbon atoms, halogenated alkoxy groups having 1 to 3 carbon atoms, monocyclic, linked or condensed rings having 6 to 20 carbon atoms Aryl group, monocyclic, linked, or condensed aryloxy group having 6 to 18 carbon atoms, monocyclic, linked, or condensed heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl having 3 to 18 carbon atoms Group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and one or more substituents selected from the group consisting of deuterium atoms). Independently, phenyl, methylphenyl, cyanophenyl, fluorophenyl, naphthylphenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 9,9-di Methylfluorenyl, dibenzothienyl, dibenzofuranyl, 9-phenylcarbazolyl, carbazolylphenyl, (9-phenylcarbazolyl) phenyl, dibenzothienylphenyl, or dibenzofuranylphenyl Groups are more preferred, and each independently represents a phenyl group, a 4-methylphenyl group, a 3-methylphenyl group, a 4-cyanophenyl group, a 3-cyanophenyl group, a 4-fluorophenyl group, a 3-fluoro Phenyl group, 4- (4-dibenzothienyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 4- (9-carbazolyl) phenyl group, 4- (9-phenylcarbazol-3-yl) phenyl group , 4-biphenyl group, 3-biphenyl group, p-terphenyl group, m-terphenyl group, 1-naphthyl group, -A naphthyl group, a 4- (1-naphthyl) phenyl group, a 3- (1-naphthyl) phenyl group, a 9,9-dimethyl-2-fluorenyl group, a 2-dibenzothienyl group, or a 2-dibenzofuranyl group. Is more preferred.

In the general formulas (1) to (5), R ^{1 to} R ³ each independently represent a monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms; A monocyclic, linked, or condensed heteroaromatic group (each of these groups independently represents a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, An ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic ring having 6 to 20 carbon atoms A linked or condensed aryl group, a C6 to C18 monocyclic, linked or condensed aryloxy group, a C3 to C20 monocyclic, linked or condensed heteroaryl group, carbon number A trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, May have one or more substituents selected from the group consisting of an ano group, a halogen atom, and a deuterium atom), a methyl group, an ethyl group, and a straight-chain, branched, or cyclic group having 3 to 18 carbon atoms. An alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a monocyclic ring having 6 to 18 carbon atoms, linking or condensing; A ring aryloxy group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom.

In R ^{1 to} R ³ , a monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms and a monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms are described. A monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms and the monocyclic, linked, or condensed heteroaromatic group having 3 to 20 carbon atoms shown in the above Ar ^{1 to} Ar ³ The group has the same definition as that of the group, and is not particularly limited, and examples thereof include the same groups as the groups shown in the above Ar ^{1 to} Ar ³ .

In R ^{1 to} R ³ , a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, or a halogenated alkyl having 1 to 3 carbon atoms Group, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, As the monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, and the halogen atom, A linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a carbon number 1-3 halogenated alkoxy groups, carbon 6-20 monocyclic, linked or condensed aryl group, 6-18 carbon monocyclic, linked or condensed aryloxy group, 3-20 carbon monocyclic, linked or condensed A heteroaryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, and the same definition as a halogen atom, which are not particularly limited. The same groups as can be exemplified.

In the general formulas (1) to (5), R ^{1 to} R ³ each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group ( These groups are each independently a methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched group having 3 to 18 carbon atoms, Or a cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, 18 monocyclic, linked or condensed aryloxy group, 3-20 carbon monocyclic, linked or condensed heteroaryl group, 3-18 carbon trialkylsilyl group, 18-40 carbon atoms A triarylsilyl group, a cyano group, A methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, which may have one or more substituents selected from the group consisting of a hydrogen atom and a deuterium atom. A methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a monocyclic, linked, or condensed aryloxy group having 6 to 18 carbon atoms, a cyano group, a deuterium atom, or It is preferably a hydrogen atom, and each is independently a phenyl group, a naphthyl group, a biphenyl group (these groups are each independently a methyl group, an ethyl group, a linear, branched, or It has at least one substituent selected from the group consisting of a cyclic alkyl group, a methoxy group, an ethoxy group, a straight-chain, branched or cyclic C3-C18 alkoxy group, a cyano group, and a deuterium atom. May be) , An ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a phenoxy group, a cyano group. Group, a deuterium atom, or a hydrogen atom, and each independently, even more preferably a phenyl group, a methyl group, a methoxy group, a cyano group, a deuterium atom, or a hydrogen atom; And it is more preferable that it is a methyl group or a hydrogen atom.

  Preferred examples of the arylamine compound of the present invention are shown below, but the invention is not limited to these compounds.

  The arylamine compound represented by the general formula (1) can be synthesized by a known method (Tetrahedron Letters, 1998, Vol. 39, p. 2367), for example, a halogen represented by the general formula (6) The compound can be synthesized by amination using a compound as a raw material in the presence of a base using a copper catalyst or a palladium catalyst.

^{(Wherein, R 1 ~R 3, Ar 1} ~Ar 3, L and X are each independently formula in (1) ^R 1 ^{to R} at ^{3, Ar} 1 ~Ar ^3, L and X as defined And each Y independently represents a halogen atom [iodine, bromine, chlorine, or fluorine].
The halogenated benzo [b] phenanthreno [9,10-d] thiophene and the halogenated benzo [b] phenanthreno [9,10-d] furan can be obtained by a known method (Angeandte Chemie International Edition, 2012). 51, 12293).

  The arylamine compound represented by the general formula (1) of the present invention can be used as a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device.

  In particular, since the arylamine compound represented by the general formula (1) has an excellent hole transporting ability, when the arylamine compound is used as a hole transporting layer and / or a hole injecting layer, a low driving voltage of the organic EL device is obtained. , High luminous efficiency, and improved durability can be realized.

  When the arylamine compound represented by the general formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL device, a known fluorescent or phosphorescent conventionally used is used in a light emitting layer. Light emitting materials can be used. The light-emitting layer may be formed with only one kind of light-emitting material, or one or more kinds of light-emitting materials may be doped in a host material.

  When forming the hole injection layer and / or the hole transport layer comprising the arylamine compound represented by the general formula (1), two or more materials may be contained or laminated as necessary. For example, oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, hexacyano A known electron accepting material such as hexaazatriphenylene may be contained or laminated.

  Further, the arylamine compound represented by the general formula (1) of the present invention can be used also as a light emitting layer of an organic EL device. When the arylamine compound represented by the general formula (1) is used as a light emitting layer of an organic EL device, the arylamine compound is used alone, is used by doping a known light emitting host material, or is known light emission. The dopant can be used after doping.

  As a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the arylamine compound represented by the general formula (1), for example, known methods such as a vacuum evaporation method, a spin coating method, and a casting method are used. Method can be applied.

  Example 1 (Synthesis of Compound (C1))

  In a 50 mL three-necked flask, 2.0 g (6.2 mmol) of compound (7), 2.1 g (6.2 mmol) of the compound represented by Amine 1, and 0.84 g of sodium-tert-butoxide (8. 7 mmol) and 20 mL of o-xylene. To the resulting slurry reaction solution, 42 mg (0.18 mmol) of palladium acetate and 132 mg (0.65 mmol) of tri (tert-butyl) phosphine were added, and the mixture was stirred at 140 ° C for 4 hours. After cooling to room temperature, 15 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 3.5 g (5.6 mmol) of a gray powder of the compound (C1) was isolated (89% yield).

  The compound was identified by FDMS measurement.

FDMS: 618
Example 2 (Synthesis of Compound (A28))

  In a 50 mL three-necked flask, 1.5 g (4.6 mmol) of compound (8), 2.2 g (4.6 mmol) of the compound represented by Amine 2, and 0.63 g of sodium tert-butoxide (6. 5 mmol), and 15 mL of o-xylene. To the obtained slurry reaction solution, 31 mg (0.13 mmol) of palladium acetate and 99 mg (0.48 mmol) of tri (tert-butyl) phosphine were added, and the mixture was stirred at 140 ° C for 6 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 3.2 g (4.2 mmol) of a pale yellow powder of the compound (A28) was isolated (yield: 92%).

  The compound was identified by FDMS measurement.

FDMS: 770
Example 3 (Synthesis of Compound (A36))

  Under a nitrogen stream, 3.0 g (9.4 mmol) of the compound (8), 7.8 g (13.2 mmol) of the compound represented by Amine 3 and 20 mL of o-xylene were added to a 50 mL three-necked flask. To the obtained slurry mixture, 42 mg (0.18 mmol) of palladium acetate and 132 mg (0.65 mmol) of tri (tert-butyl) phosphine were added, and the mixture was stirred at 140 ° C. for 6 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 7.2 g (8.2 mmol) of a pale yellow powder of the compound (A36) was isolated (87% yield).

  The compound was identified by FDMS measurement.

FDMS: 876
Example 4 (Synthesis of Compound (B21))

  In a 50 mL three-necked flask, 0.9 g (3.1 mmol) of compound (9), 1.5 g (3.1 mmol) of the compound represented by Amine 4 and 0.42 g of sodium-tert-butoxide (4. 4 mmol) and 5 mL of o-xylene. 7 mg (0.03 mmol) of palladium acetate and 21 mg (0.10 mmol) of tri (tert-butyl) phosphine were added to the obtained slurry mixture, and the mixture was stirred at 140 ° C. for 3 hours. After cooling to room temperature, 5 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 2.0 g (2.6 mmol) of a light brown powder of the compound (B21) was isolated (84% yield).

  The compound was identified by FDMS measurement.

FDMS: 754
Example 5 (Synthesis of Compound (G76))

  In a 100 mL three-necked flask, 2.9 g (9.0 mmol) of compound (10), 4.4 g (9.1 mmol) of the compound represented by Amine 5, and 1.2 g of sodium-tert-butoxide (12. 6 mmol), and 30 mL of o-xylene. 40 mg (0.18 mmol) of palladium acetate and 146 mg (0.72 mmol) of tri (tert-butyl) phosphine were added to the obtained slurry mixture, and the mixture was stirred at 140 ° C. for 6 hours. After cooling to room temperature, 30 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 6.2 g (8.0 mmol) of a pale yellow powder of the compound (G76) was isolated (89% yield).

  The compound was identified by FDMS measurement.

FDMS: 768
Example 6 (Synthesis of compound (G155))

  0.8 g (2.6 mmol) of compound (10), 1.1 g (2.6 mmol) of the compound represented by Amine 6 and 0.34 g of sodium-tert-butoxide were placed in a 50 mL three-necked flask under a nitrogen stream. .6 mmol), and 10 mL of o-xylene. To the resulting slurry mixture, 11 mg (0.05 mmol) of palladium acetate and 35 mg (0.17 mmol) of tri (tert-butyl) phosphine were added, and the mixture was stirred at 140 ° C. for 4 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene, and 1.6 g (2.2 mmol) of a pale yellow powder of the compound (G155) was isolated (84% yield).

  The compound was identified by FDMS measurement.

FDMS: 718
Example 7 (Synthesis of Compound (E85))

  In a 50 mL three-necked flask, 0.38 g (1.2 mmol) of compound (11), 0.52 g (1.2 mmol) of the compound represented by Amine 7, and 0.16 g of sodium-tert-butoxide (1) were placed under a nitrogen stream. 0.7 mmol) and 5 mL of o-xylene. To the obtained slurry mixture, 2 mg (0.01 mmol) of palladium acetate and 8 mg (0.04 mmol) of tri (tert-butyl) phosphine were added, and the mixture was stirred at 140 ° C. for 2 hours. After cooling to room temperature, 5 mL of pure water was added and stirred. The product precipitated in the organic layer was collected by filtration and washed with water and ethanol. The obtained brown powder was recrystallized from o-xylene to isolate 0.66 g (0.91 mmol) of a yellow powder of the compound (E85) (yield: 76%).

  The compound was identified by FDMS measurement.

  FDMS: 718

  The arylamine compound of the present invention can be used as a light emitting material, a hole injection material, or a hole transport material of an organic EL device. In particular, the arylamine compound of the present invention is useful as a hole-injecting material or a hole-transporting material because of its excellent hole-transporting ability.

  Further, the arylamine compound of the present invention is applied not only to a hole injection material or a hole transport material of an organic EL element or an electrophotographic photosensitive member, but also to an organic device such as an organic thin-film solar cell, an organic transistor, or an image sensor. Is also possible.

Claims (9)

An arylamine compound represented by the general formula (1).

(In the formula, X represents an oxygen atom or a sulfur atom.
L is a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms [these Are each independently a methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or 3 to 18 carbon atoms. Cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, 6 to 18 carbon atoms A monocyclic, linked or condensed aryloxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a C18 to C40 From triarylsilyl, cyano, halogen and deuterium atoms That represents the more the substituents may be one or more selected] group.
Ar ^{1 to} Ar ³ each independently represent a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked or condensed heterocyclic group having 3 to 20 carbon atoms. Aromatic group [These groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A chain, branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, A monocyclic, linked, or fused aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked, or fused heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, carbon A triarylsilyl group, a cyano group, and a halogen atom represented by Formulas 18 to 40 And it represents deuterium consisting atom a substituent selected from the group may have one or more.
R ^{1 to} R ³ each independently represent a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 20 carbon atoms, a monocyclic, linked, or fused heteroaromatic having 3 to 20 carbon atoms. Group [These groups each independently represent a methyl group, an ethyl group, a linear or branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, carbon A monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a carbon number 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and heavy May have one or more substituents selected from the group consisting of elemental atoms], a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, and an ethoxy group. A linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, carbon number Represents a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. ) The arylamine compound according to claim 1, wherein the arylamine compound represented by the general formula (1) is an arylamine compound represented by any of the following general formulas (2) to (5).

(In the formula, X, L, Ar ^{1 to} Ar ³ , and R ^{1 to} R ³ are the same as in claim 1.) Ar ^{1 to} Ar ³ each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a benzofluorenyl group, a dibenzothienyl group, a dibenzofuranyl group, a carbazolyl group; Group, carbazolylphenyl group, dibenzothienylphenyl group, or dibenzofuranylphenyl group (these groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic group having 3 to 18 carbon atoms) Alkyl group, methoxy group, ethoxy group, C3-18 linear, branched or cyclic alkoxy group, C1-3 halogenated alkyl group, C1-3 halogenated alkoxy group, carbon number 6-20 monocyclic, linked or condensed aryl groups, 6-18 carbon monocyclic, linked or condensed aryloxy groups, 3 carbon atoms 0 monocyclic, linked or condensed heteroaryl group, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group, halogen atom, and deuterium atom The arylamine compound according to claim 1, wherein the arylamine compound is a substituent represented by the following formula: Ar ^{1 to} Ar ³ each independently represent a phenyl group, a methylphenyl group, a cyanophenyl group, a fluorophenyl group, a naphthylphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, 9,9 -Dimethylfluorenyl, dibenzothienyl, dibenzofuranyl, 9-phenylcarbazolyl, carbazolylphenyl, (9-phenylcarbazolyl) phenyl, dibenzothienylphenyl, or dibenzofuranyl The arylamine compound according to any one of claims 1 to 3, wherein the arylamine compound is a substituent represented by a phenyl group.   L represents a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthracene-diyl group, or a fluorene-diyl group (these groups are each independently a methyl group, an ethyl group, a straight-chain having 3 to 18 carbon atoms). Chain, branched or cyclic alkyl group, methoxy group, ethoxy group, C3-18 straight, branched or cyclic alkoxy group, C1-3 halogenated alkyl group, C1-3 Halogenated alkoxy group, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, monocyclic ring having 3 to 20 carbon atoms , A linked or condensed heteroaryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. Arylamine compound of claim 1 to claim 4 any one, characterized in that substituent is which may have 1 or more). R ^{1 to} R ³ each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group (these groups each independently represent a methyl group, an ethyl group, a C 3-18 Straight-chain, branched or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched or cyclic alkoxy group, C1-C3 halogenated alkyl group, C1-C3 A halogenated alkoxy group, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, a monocyclic group having 3 to 20 carbon atoms Selected from the group consisting of a ring, a linked or condensed heteroaryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. Has at least one substituent ), A methyl group, an ethyl group, a straight-chain, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or cyclic alkoxy group having 3 to 18 carbon atoms. 6. A monocyclic, linked or condensed aryloxy group, a cyano group, a deuterium atom, or a hydrogen atom having 6 to 18 carbon atoms, wherein: The arylamine compound according to item. R ¹ to R ^3, characterized in that each independently a methyl group or a hydrogen atom, an aryl amine compound according to any one of claims 1 to 6. An organic EL device containing the arylamine compound represented by the general formula (1).

(In the formula, X represents an oxygen atom or a sulfur atom.
L is a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms [these Are each independently a methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or 3 to 18 carbon atoms. Cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, 6 to 18 carbon atoms A monocyclic, linked or condensed aryloxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a C18 to C40 From triarylsilyl, cyano, halogen and deuterium atoms That represents the more the substituents may be one or more selected] group.
Ar ^{1 to} Ar ³ each independently represent a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked or condensed heterocyclic group having 3 to 20 carbon atoms. Aromatic group [These groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A chain, branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, A monocyclic, linked, or fused aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked, or fused heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, carbon A triarylsilyl group, a cyano group, and a halogen atom represented by Formulas 18 to 40 And it represents deuterium consisting atom a substituent selected from the group may have one or more.
R ^{1 to} R ³ each independently represent a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 20 carbon atoms, a monocyclic, linked, or fused heteroaromatic having 3 to 20 carbon atoms. Group [These groups each independently represent a methyl group, an ethyl group, a linear or branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, carbon A monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a carbon number 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and heavy May have one or more substituents selected from the group consisting of elemental atoms], a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, and an ethoxy group. A linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, carbon number Represents a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. ) A material for an organic EL device containing the arylamine compound represented by the general formula (1).

(In the formula, X represents an oxygen atom or a sulfur atom.
L is a monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked, or condensed divalent heteroaromatic group having 3 to 20 carbon atoms [these Are each independently a methyl group, an ethyl group, a straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight-chain, branched, or 3 to 18 carbon atoms. Cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, 6 to 18 carbon atoms A monocyclic, linked or condensed aryloxy group, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a C18 to C40 From triarylsilyl, cyano, halogen and deuterium atoms That represents the more the substituents may be one or more selected] group.
Ar ^{1 to} Ar ³ each independently represent a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 20 carbon atoms, or a monocyclic, linked or condensed heterocyclic group having 3 to 20 carbon atoms. Aromatic group [These groups each independently represent a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A chain, branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, A monocyclic, linked, or fused aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked, or fused heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, carbon A triarylsilyl group, a cyano group, and a halogen atom represented by Formulas 18 to 40 And it represents deuterium consisting atom a substituent selected from the group may have one or more.
R ^{1 to} R ³ each independently represent a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 20 carbon atoms, a monocyclic, linked, or fused heteroaromatic having 3 to 20 carbon atoms. Group [These groups each independently represent a methyl group, an ethyl group, a linear or branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a linear group having 3 to 18 carbon atoms. A branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryl group having 6 to 20 carbon atoms, carbon A monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, a monocyclic, linked or condensed heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, and a carbon number 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and heavy May have one or more substituents selected from the group consisting of elemental atoms], a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, and an ethoxy group. A linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a monocyclic, linked or condensed aryloxy group having 6 to 18 carbon atoms, carbon number Represents a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )